Acetic Acid → Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxybutyrate

HRID 280971ノート

反応式

HRID 280971 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][C:19](=[O:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.C(O)C.C([BH3-])#N.[Na+]>O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH:19]([OH:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 702EthanolHCID 5003444Sodium cyanoborohydrideHCID 19868897Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-oxobutyrate

生成物 1

HCID 20143718Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxybutyrate収率 67.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a stirred mixture of ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-oxobutyrate (17 g), acetic acid (4.5 g) and ethanol (30 ml) is added sodium cyanoborohydride (3 g) at room temperature. After stirring for 3 hours at room temperature, the mixture is diluted with water (500 ml) and extracted with methylene chloride. The organic extract is dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue is purified by silica gel column chromatography using hexane-ethyl acetate (2:1-1:1) as an eluent to give ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxybutyrate (11.5 g) as a colorless oil.

後処理

  1. extractionextracted with methylene chloride
  2. extractionThe organic extract
  3. dry with materialis dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-091866747c6844f5a619ab91a57931bd
出典データセット
uspto-grants-1986_05
特許番号
US04591458

反応ノート

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